反应 #1914848

反应方程式

3,5-Dichloroanisole

magnesium

N,N-dimethylformamide

→

sub-title compound

收率 54.0%

3-Chloro-5-methoxybenzaldehyde

收率 54.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   温度The resultant dark brown mixture was heated
3. 3
   温度at reflux for 3 h
4. 4
   其他The mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL)
5. 5
   洗涤The combined organic extracts were washed with brine (300 mL)
6. 6
   干燥dried (Na2SO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他to give an oil
10. 10
    其他Flash chromatography (2×) on silica get
11. 11
    洗涤eluting with Hex

实验过程

3,5-Dichloroanisole (74.0 g, 419 mmol) in THF (200 mL) was added dropwise to magnesium metal (14.2 g, 585 mmol, pre-washed with 0.5 N HCl) in THF (100 mL) at 25° C. After the addition, 1,2-dibromoethane (3.9 g, 20.8 mmol) was added dropwise. The resultant dark brown mixture was heated at reflux for 3 h. The mixture was cooled to 0° C., and N,N-dimethylformamide (60 mL) was added in one portion. The mixture was partitioned with diethyl ether (3×400 mL) and 6N HCl (500 mL). The combined organic extracts were washed with brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography (2×) on silica get eluting with Hex:EtOAc (4:1) afforded the sub-title compound (38.9 g, 54%) as a yellow oil.

来源